Sodium Iodide → 6-(3-Phthalimidopropoxy)carbostyril

HRID 1856747Notes

Reaction equation

HRID 1856747 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]2.[I-].[Na+].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K]>CN(C)C=O>[C:19]1(=[O:29])[N:23]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]3)[C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 142894806-(3-Chloropropoxy)carbostyrilHCID 24194345Phthalimide potassium salt

Product 1

HCID 117724126-(3-Phthalimidopropoxy)carbostyrilYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 6-(3-chloropropoxy)carbostyril (170 g) and sodium iodide (129.5 g) in dimethylformamide (1.7 liter) is heated with stirring at 60° C. for one hour. To the mixture is added potassium phthalimide (159 g), and the mixture is heated with stirring at 70° C. for 6 hours. After the mixture is allowed to cool, the precipitated crystals are collected by filtration, and washed with water. The mixture is further washed successively with ethanol and diethyl ether, and dried to give 6-(3-phthalimidopropoxy)carbostyril (222 g) as a white powder.

Workup

  1. temperatureis heated
  2. temperaturethe mixture is heated
  3. stirringwith stirring at 70° C. for 6 hours
  4. temperatureto cool
  5. filtrationthe precipitated crystals are collected by filtration
  6. washwashed with water
  7. washThe mixture is further washed successively with ethanol and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-5d19e8e15c76498aba3ff1b29ef9061b
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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